Sort by
Relevancy

Free Stories

100%
Being Shemale Part II
After sometime the driver left. Night Two I was again ready by 10 Pm as usual wearing make up and sexy night outfit. My push up bra helped my breast look very attractive looked perfect with my slim body I was standing as usual in the balcony around 11 PM and the driver stopped by again.... Read full Story
babydriver 2024-06-04 2,756 Amateur Shemale Fucks Guy Big Cock Asian Ladyboy Lingerie domination small cock big ass Frottage sissy femboy
100%
My shemale initiation
I was alone at home. Wife gone for a vacation. I was surfing the net. I am infatuated with shemales. I looked at redbook and saw a very sexy lady. I contacted her. I drove to her hotel and picked her up. She was gorgeous. As we drove to my house, I asked about the size of her package. She said 9". I... Read full Story
shedawg 2022-04-04 5,547 Amateur Shemale Fucks Guy cum in mouth
85%
My Knight
I felt good as a looked around the club and watch the Queens on stage perform their acts. I felt like I belonged here among this faction of society. Drag queens and Trannies were my people and the only thing I regret is being in the closet and not having the courage to do it more openly. However i d... Read full Story
Regina10 2020-06-23 3,854 Bareback Guy Fucks Shemale Ass to Mouth shemale + shemale
100%
Mein Traum 2
Hallo mein Gebieter, ich hatte einen Traum. Darin gehe ich mal wieder ins Duplexx in der Schönhauser Allee. Nach einigem Cruisen bleibe ich in einer Kabine stehen, lasse die Tür offen und stelle mich mit dem Rücken zum Eingang vor den Monitor. Ich gucke einen Shemale-Streifen und spiele etwas an ... Read full Story
Jasmin_P 2021-03-02 2,016 Amateur Group Sex Bareback Creampie Fetish threesome gangbang domination Guy Fucks Shemale rimjob Ass to Mouth piss drinking cum in mouth
71%
The story of how I became what I am now...
I was on a trip to Germany with some of my friends. I was 16 when this happened. We went to a club one night and I got really drunk. They challenged me to approach a cute girl and ask her for a drink with me. I was drunk so I didn't really care so I went there and bought her a drink. We talked and I... Read full Story
FeetQueen 2019-01-08 5,470 Stockings Teen (18+) Small Tits Amateur Shemale Fucks Guy Lingerie Homemade cum in mouth
54%
My lifes story, which I want to share it with world!
Since my childhood very beginning every time when I see female to which I am attracted to, I imagine how I would go down on her, I just love to do enjoying it for hours. I am obsessed with cunnilingus and I do it with passion!... and then this happened... I'm still writing my full movie scene abo... Read full Story
Sanitaladyboy 2020-09-02 3,792 Stockings Crossdresser Amateur Group Sex Shemale Fucks Guy Fetish threesome Big Cock Ladyboy Lingerie domination Sex Toys
75%
A Big thank you to everyone and what's to come next year!
Hi everyone! This is something of a yearly wrap up that I wanted to write up. First I wanted to thank you all for following me this year ❤️ This was the first year that I decided to start taking this seriously and create content full time. I think I still have a ways to go to improve my content, but... Read full Story
Kate Quinn 2022-12-31 3,321 Amateur Big Tits Big Cock Shemale and Girl Guy Fucks Shemale
41%
My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
bmogotti 2020-03-09 13,120 anal first time Small Tits Crossdresser Amateur Blowjob shemale Big Cock Ebony fuck Lingerie Guy Fucks Shemale Homemade motel
83%
the start of what to cum
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often mo... Read full Story
oliviabecket23 2023-07-04 6,778 Crossdresser Lingerie domination Sex Toys femboy forced webcams
83%
She came inside of me
In my city there are several transsexual brothers where there are usually a good amount of attractive girls working. It had been quite a while since I've visited one but on a hot sunday night I decided to pay one of them a visit. Even though I had been here before I was nervous, the place is... Read full Story
Gracemel121 2017-07-18 17,838 Amateur Shemale Fucks Guy
50%
My Shemale Sex Adventures
Fresh meat Kevin Judd submits to hot top Korra Del Rio in this sexy Valentines Day special. Sensual domination is Goddess Korra's forte and oh boy does she deliver once she gets her hands on this new submissive slut Kevin. Decked out in seductive, strappy black lingerie, thigh high stockings and hee... Read full Story
KevinRichardJudd 2020-06-16 4,123 Shemale Fucks Guy
100%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 6,157 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
92%
Shemale sex on a beach
Had to tell you what happened to me recently. I wrote to one of my favourite shemales last week and was telling her I missed sucking and fucking with her due to the current virus situ. Wished I could travel to see her and have some fun and she told me she was away from home too. I asked her where an... Read full Story
xanykeyx 2020-05-07 8,784 suck Outdoor Shemale Fucks Guy shemale cum fuck orgasm Guy Fucks Shemale sex climax deep beach sex
100%
TSA and TS lady
While traveling through Tamp Florida one visit to see my very good friends, I of course, as all travelers on airlines these days do, had to clear a TSA security check point. Dressed in a pair of tights and a T-shirt and pair of sneaker with low rise socks, pretty easy and relaxed for a couple of hou... Read full Story
Jamie Sinns 2021-10-11 2,985 solo Amateur Big Cock Homemade Shemale and TSA Shemale examination Shemale inspection Shemale Approval Shemale travels alone
80%
Fucked by Priscilla Gaucha
This black woman always drove me crazy, I always liked her photos and videos on the internet. Unfortunately, when I had the courage to face it, she moved out of state and ended up being left in the lurch. However, one night driving by, I came across her. She was beautiful, strong thighs, well made-... Read full Story
mauricioportoalegre 2024-05-09 3,373 anal Amateur Shemale Fucks Guy Big Cock Ebony
100%
My Afternoon With Venus - Part I
It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... Read full Story
funpics 2018-03-23 13,146 Amateur Shemale Fucks Guy Asian Guy Fucks Shemale Homemade
88%
Steamy date with a TS
Last year I had a great experience with a TS escort and I saw she was in town again, I texted her to meet for dinner and to my surprise she agreed. I met her at the restaurant and we had a nice time together, she´s very friendly and incredibly attractive. She wore a red summer dress with high hee... Read full Story
Gracemel121 2018-08-27 9,885 Amateur Shemale Fucks Guy domination Ass to Mouth
97%
Shemale fucks guy - My gf fucks my slutty ass.
I have a shemale girlfriend & we both are in a relationship. One day, I decide to give her a visit. I'm 5'7 guy & she's 6 feet. That makes her tall & intimidating & whenever we meet, it's me who become her gf. I visit her, she takes me in. SHe pulls me towards her while giving me a deep kiss. I ... Read full Story
glodobox 2020-12-04 22,287 Amateur Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Ladyboy Homemade cum in mouth
75%
So good fuck with me and my klients.
Hello, I am Francesca, and I offer company to couples and women. A few days ago, a couple hired me for two hours.The woman was fucking me with her strapon while I was stroking the man's cock. She was pushing her hard cock deeper and inside me, I could feel my ass dissolving more and more. I turn my ... Read full Story
Francheskahotass 2021-08-11 3,370 Crossdresser Amateur Group Sex Cumshot Shemale Fucks Guy threesome Ladyboy Lingerie Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,659 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
90%
Why does cock look so good on a girl ?
Horny and looking for something to jerk off on, of started surfing porn sites looking for just the right hottie. Pornstar Christie Lee really gets my juices going so I clicked on her. I started watching the video I was familiar with and knew would get me off when I decided to check out all her video... Read full Story
Verdura08 2022-10-17 6,172 Crossdresser Amateur Cumshot Big Cock ts posing huge dildo
50%
MA MAÎTRESSE MIRACLE
Sam tapota nerveusement ses doigts contre le verre à moitié plein. En règle générale, vous êtes censé boire un coup avec une gorgée, mais sa tolérance à l'alcool n'était pas exactement la meilleure et le bourbon dans la tasse servait vraiment plus de courage liquide à ce stade. Cela faisait ... Read full Story
Femboy 2021 2023-02-05 1,150 Stockings domination Sex Toys Futanari Ass to Mouth cum in mouth shemale + shemale
100%
FUTA UNIVERSITY BOY-JOUET
L'interphone du bureau de Jane Johnson bourdonna. "Oui, Mary," dit Jane. "Il y a une Mme Winter ici pour vous voir madame." Marie a répondu. "Par tous les moyens, envoyez-la directement." dit joyeusement Jane. La porte du bureau du principal a été ouverte par ... Read full Story
Femboy 2021 2023-02-10 1,034 Stockings Big Cock Lingerie domination Futanari cum in mouth shemale + shemale
16%
Current Fantasy
I really wanna get fucked for the first time and my dream way of doing it, always wanted to do a porn. The dream is that I go there and get done up in such a way, I am unrecognizable, just looking the best. Have a tranny come in and do my make up, the way she likes it and gives me a preview of what ... Read full Story
martley 2023-06-30 5,293 anal Amateur Group Sex Cumshot Fetish Big Cock Lingerie big ass Homemade femboy shemale fucks shemale cum in mouth
50%
Me & Jo Shemale
Yesterday Jo Shemale and I went for on a pussy hunting fall walk. Well, I did, I'm pretty sure Jo Shemale wasn't hunting pussy. It was getting colder, so we had to put on our woolly panties and sweaters. Halfway down the block, we saw the Old Fuck's out in their yard. The Old Fuck's were raking b... Read full Story
shemale lover 2011-08-16 4,624 cock suck shemale
81%
First time shemale encounter
Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... Read full Story
iloveshemales112 2011-12-17 9,476 Latina Bareback Shemale Fucks Guy Big Cock
100%
Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
shemale lover 2012-02-06 5,241 sucking shemale massage
95%
My First Time
I used to be a normal straight guy, or at least, so I thought. That was until I began exploring trans porn, I was so turned on by it, but thought it was wrong, I tried to fight it, but soon enough trans porn became the only porn I could get off to. I didn't know what to do with this obsession, ... Read full Story
handsome man 2018-06-07 22,046 Crossdresser Amateur Shemale Fucks Guy Sex Toys Homemade cum in mouth
88%
LONDON CINEMA LIAISON
When I lived in London back in the 80s and 90s, I would often sneak off to a porn cinema with stockings, suspenders and knickers under my suit. My wife didn’t much like sex, so this was a release for me to get away from home and have some sexy fun. Once I had found a suitable seat I would ease down ... Read full Story
GinaG 2018-12-14 7,114 Stockings Blowjob blonde Lingerie Guy Fucks Shemale Mature Ass to Mouth
54%
Experience with Shemale Kadambari in Pune
PS: this is a genuine experience. Hey, I am back with another story. Let me introduce myself. I am ordinary guy who like to score shemale from Pune. I have already posted one experience with arzoo. So yes let's start, I had a normal chat with Kadambari on what's app discussing the rates. So she a... Read full Story
spidymoto 2020-03-24 6,434 Cumshot Blowjob shemale Big Cock Guy Fucks Shemale indian Indian Shemale Pune Pune Shemale
50%
The BIG COCK that I will eat.
ENGLISH: Hello friends. In the link below, you can see the tranny cock that will fuck me in the days to come. I saw her advertised on the internet, I picked up the phone and called, I will see her when her clinical tests are negative for sexually transmitted diseases, because I will surely swallow... Read full Story
cuchillo 2020-09-18 7,727 Amateur Cumshot Latina Shemale Fucks Guy Blowjob Big Cock Homemade cum in mouth brunette ts swallow cum
100%
TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
SpankydeBautumn 2021-02-22 3,663 Small Tits Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
100%
TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
SpankydeBautumn 2021-02-23 2,532 Small Tits Crossdresser Amateur Cumshot Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
75%
My first night was making love to a man
First .... My name is Lely Bella Calistia, of course it's the name when I decided to become Shemale. My age is now 28th, I became a shemale when I was 24th, when I first chose to be a shemale because I was obsessed with my ex girlfriend, after parting ,, .. maybe because I really miss her an... Read full Story
Bella Calis 2018-03-13 9,396 Amateur Asian Guy Fucks Shemale
33%
My new Experience with Amy Cute Shemale in Pune
Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... Read full Story
Stud4Shemale 2021-02-20 6,182 Cumshot Bareback Creampie Shemale Fucks Guy Blowjob Asian Guy Fucks Shemale shemale fucks man man-fucking-shemale Indian Shemale Pune
100%
My wonderful life with Pat : Pat birthday
Today we will received a friend of Pat for her birthday Charles and Pat are friends since the kindergarden Today Charles is married with Suzanne. Charles has followed the Pat sexual changes from young man to lady shemale. Before being with Suzanne Michel had participated to several parties... Read full Story
jperrot 2021-07-21 3,166 Amateur Outdoor threesome Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth